Ethyl 2-chloro-2-(hydroxyimino)acetate → HCID 9861448, compound

HRID 1267222Notes

Reaction equation

HRID 1267222 reaction equation
[CH2:1]([CH:4]1[N:10]2[C:11](=[O:14])[O:12][N:13]=[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH3:15][CH2:16][O:17][C:18](/[C:20](/Cl)=[N:21]\[OH:22])=[O:19]>C1(C)C=CC=CC=1>[O:14]=[C:11]1[N:10]2[CH:4]([CH2:1][CH:2]3[O:22][N:21]=[C:20]([C:18]([O:17][CH2:16][CH3:15])=[O:19])[CH2:3]3)[CH2:5][CH2:6][CH2:7][CH2:8][C:9]2=[N:13][O:12]1

Participants

4

Reactant 2

HCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetateHCID 9815533HCID 9815533, compound

Product 1

HCID 9861448HCID 9861448, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 0.5 g (2.6 mmol) of the product of Example 6 in 100 mL of toluene was added 0.8 g (5.2 mmol) of ethyl chlorooximidoacetate (Aldrich). This solution was brought to reflux and stirred for 18 hours. All solvent was removed in vacuo and the residue purified via C-18 chromatography (0-60% acetonitrile/water, 25 min.) with the product eluting at 54% acetonitrile. Concentration of the relevant fractions afforded 0.6 g (75% yield) of the title compound as a pale yellow oil.

Workup

  1. temperatureto reflux
  2. customAll solvent was removed in vacuo
  3. customthe residue purified via C-18 chromatography (0-60% acetonitrile/water, 25 min.) with the product
  4. washeluting at 54% acetonitrile

Sources & evidence

ORD record
ord-d2ee6ce3173c42a18558a37f80d47699
Source dataset
uspto-grants-2003_04
Patent number
US06552052B2

Reaction notes

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